Also, be sure to compare the resort's insurance with private insurance, using a service such as insuremytrip.com. Generally, you're better off with the resort's insurance only when they insure something that a private insurer will not insure, such as is the case with DVC points. Also, keep in mind that the value of freebies and the specific amount of discounts generally cannot be insured. (You can get some coverage for being displaced, but that's not the same as having the amount of the discount insured.)
I've found that I'm much better off financially self-insuring, based on how much it costs to buy insurance, how often I incur a loss, how much loss, and how much insurance would cover in case of loss. It might make you cringe to break out the credit card to pay full-fare to get you and your family home in case the worst happens, but unless your credit card doesn't have that much credit on it, taking that risk is, in the long-run, going to be a better financial deal than buying insurance.
By the same token, when I'm on a cruise, my credit card CANNOT cover the cost of a medical evacuation, so I always purchase
travel insurance on a cruise.